Chittenden holiday rentals

We found 1,058 holiday rentals — enter your dates for availability
Discover a selection of 10 homes and other holiday rentals in Chittenden that are perfect for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll have the best amenities for spending time at your home away from home, which might include parking and a fireplace. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Chittenden

Showing deals for:18 Dec - 25 Dec

Living Room with access to back porch
5 person salt water hot tub
Kitchen
Fully stocked eat-in kitchen
Exceptional
(27 reviews)

Spacious And Beautiful Luxury Home In Killington

Killington

8% off
AU$11,790
for 7 nights, 1 home
AU$1,684 per night
includes taxes & fees
Spacious And Beautiful Luxury Home In Killington
Living area
Sun Room
Dining
Interior
Exceptional
(11 reviews)

Luxury 4 Bedroom Ski Retreat Near Killington, Pico & Mountain Top Inn.

Rutland

8% off
AU$10,976
for 7 nights, 1 home
AU$1,568 per night
includes taxes & fees
Luxury 4 Bedroom Ski Retreat Near Killington, Pico & Mountain Top Inn.
Family room with gas fireplace, Frame TV, Sonos over Vermont barn mantle.
Terrace/patio
Exterior
Private kitchen
Exceptional
(97 reviews)

5 BR 3.5 Bath Killington Home with Hot Tub, Huge Dining Table, Summer Pool

Killington

8% off
AU$16,584
for 7 nights, 1 home
AU$2,369 per night
includes taxes & fees
5 BR 3.5 Bath Killington Home with Hot Tub, Huge Dining Table, Summer Pool
lots of room to relax in front of fireplace
Pool
Fitness facility
Interior
Exceptional
(56 reviews)

Multi-Level Slopeside Townhouse End Unit in Sunrise's Timberline Section

Killington

8% off
AU$11,286
for 7 nights, 1 home
AU$1,612 per night
includes taxes & fees
Multi-Level Slopeside Townhouse End Unit in Sunrise's Timberline Section
Room
Interior
Exterior
Living area
Exceptional
(105 reviews)

Luxury Ski House on Killington Mtn, 2 beds & Den w/ 3 en-suite baths, hot tub

Killington

8% off
AU$10,379
for 7 nights, 1 home
AU$1,483 per night
includes taxes & fees
Luxury Ski House on Killington Mtn, 2 beds & Den w/ 3 en-suite baths, hot tub
Exterior
Dining
Private kitchen
Living area
Exceptional
(29 reviews)

North Porch Farmhouse

Rochester

8% off
AU$3,130
for 7 nights, 1 home
AU$447 per night
includes taxes & fees
North Porch Farmhouse
Lower Level Bar/Kitchenette
Image from trailhead
Living Room - looking out over mountains
Bedroom 3 - queen bed
Exceptional
(67 reviews)

Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

Killington

8% off
AU$14,619
for 7 nights, 1 home
AU$2,088 per night
includes taxes & fees
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated
Living Room w/propane 'fireplace'
View from driveway
Mud room view to dining room
Beverages optional
Exceptional
(65 reviews)

Killington Skiers/Snowmobilers/MountainBikers Dream with Outdoor Jacuzzi + Wi-Fi

Stockbridge

8% off
AU$6,570
for 7 nights, 1 home
AU$939 per night
includes taxes & fees
Killington Skiers/Snowmobilers/MountainBikers Dream with Outdoor Jacuzzi + Wi-Fi
Exterior detail
Living room
Living Room
view from the Foundry
Exceptional
(61 reviews)

Private Mountain View minutes to Hiking, biking, golfing, skiing, snowboarding

Killington

9% off
AU$10,530
for 7 nights, 1 home
AU$1,504 per night
includes taxes & fees
Private Mountain View minutes to Hiking, biking, golfing, skiing, snowboarding
Living area
Interior
Dining
Terrace/patio
Exceptional
(9 reviews)

5 Min to Lodges & Town; Arcade & Ping Pong Table; Hot Tub; Renovated

Killington

8% off
AU$12,782
for 7 nights, 1 home
AU$1,826 per night
includes taxes & fees
5 Min to Lodges & Town; Arcade & Ping Pong Table; Hot Tub; Renovated
Exterior
Outdoor dining
Interior
Private kitchen
Exceptional
(125 reviews)

Waterfront Ponds, Beautiful , 51 Acre Property Retreat

Brandon

7% off
AU$2,839
for 7 nights, 1 home
AU$406 per night
includes taxes & fees
Waterfront Ponds, Beautiful , 51 Acre Property Retreat
Kitchen
Kitchen
Living area
Living room
Exceptional
(17 reviews)

Base Camp Retreat at Killington - Trails, Hot Tub, Fire Pit & Game Room

Killington

8% off
AU$10,865
for 7 nights, 1 home
AU$1,552 per night
includes taxes & fees
Base Camp Retreat at Killington - Trails, Hot Tub, Fire Pit & Game Room
Dining
beautiful arial view of Sunrise in the fall
work out room at Sunrise
Outdoor pool in summer months
Exceptional
(49 reviews)

True ski in/out condo at The Lodges - Trailside Luxury w/ pool & hot tub access

Killington

8% off
AU$12,688
for 7 nights, 1 apartment
AU$1,813 per night
includes taxes & fees
True ski in/out condo at The Lodges - Trailside Luxury w/ pool & hot tub access
Living area
Outdoor dining
Interior
Living area
Exceptional
(7 reviews)

VT Lodge Cabin w Mountain Views near Killington

Proctor

8% off
AU$5,401
for 7 nights, 1 cabin
AU$772 per night
includes taxes & fees
VT Lodge Cabin w Mountain Views near Killington
Living area
Living area
Interior
Exterior
Exceptional
(6 reviews)

Breathtaking Views & Walking Distance to the Fabulous Mountain Top Inn Resort

Chittenden

8% off
AU$8,279
for 7 nights, 1 home
AU$1,183 per night
includes taxes & fees
Breathtaking Views & Walking Distance to the Fabulous Mountain Top Inn Resort
Pool
Living area
Interior
Exterior
Exceptional
(30 reviews)

3 Bed 3 Bath Luxury Ski-In/Ski-out Condo Killington Sunrise Village Slopeside

Killington

8% off
AU$11,276
for 7 nights, 1 apartment
AU$1,611 per night
includes taxes & fees
3 Bed 3 Bath Luxury Ski-In/Ski-out Condo Killington Sunrise Village Slopeside
Living room with cathedral ceiling, wood-burning fireplace, and 50" TV
Living area
Private kitchen
Mud-room, with firewood and kindling provided
Exceptional
(14 reviews)

Spacious Townhouse on the Killington Access Road

Killington

10% off
AU$7,599
for 7 nights, 1 home
AU$1,086 per night
includes taxes & fees
Spacious Townhouse on the Killington Access Road
Pool area completely renovated in 2024
Exterior
Two large hot tubs!! Perfect after a cold day skiing!
View from Balcony
Exceptional
(47 reviews)

Killington Condo Penthouse Mountain View Underground parking Pool Hot Tub - 3F10

Killington

7% off
AU$4,399
for 7 nights, 1 apartment
AU$628 per night
includes taxes & fees
Killington Condo Penthouse Mountain View Underground parking Pool Hot Tub - 3F10
View from the parking lot.
Pool
Interior
Entrance to The Woods Resort & Spa
Exceptional
(104 reviews)

Luxury 'Exec' Condo with Spa, Indoor Pool, Hot Tubs, Sauna -

Killington

7% off
AU$3,803
for 7 nights, 1 apartment
AU$543 per night
includes taxes & fees
Luxury 'Exec' Condo with Spa, Indoor Pool, Hot Tubs, Sauna -
washer and dryer
open floor plan
Interior
Interior
Exceptional
(9 reviews)

The mountains are calling! Renovated 2 Bdrm 3 Bath 4 queen beds close to all

Killington

12% off
AU$6,737
for 7 nights, 1 apartment
AU$962 per night
includes taxes & fees
The mountains are calling! Renovated 2 Bdrm 3 Bath 4 queen beds close to all
Terrace/patio
Living area
Living area
Private kitchen
Exceptional
(9 reviews)

Killington condo 5 min to killington resort

Killington

6% off
AU$2,183
for 7 nights, 1 apartment
AU$312 per night
includes taxes & fees
Killington condo 5 min to killington resort
New Stainless steel appliances with Bosch convection oven
Dining
The appliances were updated to stainless steel
Room
Exceptional
(15 reviews)

Powder Stash Large 1 Bedroom 2 full baths 2 queen beds and queen sleeper sofa

Killington

12% off
AU$3,142
for 7 nights, 1 apartment
AU$449 per night
includes taxes & fees
Powder Stash Large 1 Bedroom 2 full baths 2 queen beds and queen sleeper sofa
Heated pool in the summer months
Car charging available
LED bulbs
Property grounds
Exceptional
(33 reviews)

Studio with two queen beds renovated on bus route close to all

Killington

12% off
AU$2,087
for 7 nights, 1 apartment
AU$298 per night
includes taxes & fees
Studio with two queen beds renovated on bus route close to all

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Explore the majestic setting in Chittenden

The mountains and lake provide a pleasant backdrop to your holiday home in Chittenden. This romantic and scenic city is well known for its skiing, sledging and bars. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Chittenden

Are you looking for things to do while you're in town? Venture out of your holiday home and check out everything that makes Chittenden a one-of-a-kind holiday spot. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Green Mountain National Golf Course (6.2 mi / 10 km)
  • Pico Mountain at Killington Ski Resort (7.4 mi / 11.9 km)
  • Killington Resort (10.1 mi / 16.2 km)
  • Killington Golf Course (10.1 mi / 16.3 km)
  • Pond Hill Ranch and Pro Rodeo (14.9 mi / 24 km)
  • Saskadena Six Ski Area (20.3 mi / 32.6 km)

Exploring the natural landscape of Chittenden

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Chittenden is a great spot to appreciate mother nature. These are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Pico Peak (8.1 mi / 13 km)
  • Killington Peak (10.4 mi / 16.8 km)
  • Lake Hortonia (13.1 mi / 21.1 km)
  • Lake Dunmore (13.8 mi / 22.2 km)
  • Lake Bomoseen (14.8 mi / 23.8 km)
  • Silver Lake State Park (16.5 mi / 26.5 km)

Transport options to and around Chittenden

The nearest airport is in Rutland, VT (RUT-Rutland Southern Vermont Regional), located 13.8 mi (22.2 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into Lebanon, NH (LEB-Lebanon Municipal), which is 32.5 mi (52.2 km) away.

Frequently asked questions

What is the best area to stay in Chittenden when booking a holiday rental?
When considering a holiday rental in Chittenden, Vermont, the area around the picturesque Chittenden Reservoir is an excellent choice. This scenic spot not only provides stunning views and a tranquil atmosphere but also offers access to various outdoor activities such as kayaking, fishing, and hiking. The surrounding area is dotted with charming properties, with a mix of rustic cabins and modern cottages that cater to different tastes and budgets.Another appealing option is the vicinity of the Green Mountain National Forest, which is renowned for its breathtaking landscapes and extensive trails. This area is superb for those who enjoy exploring nature, with opportunities for hiking, birdwatching, and even winter sports during the colder months. Along with its natural beauty, the forest is close to some delightful local attractions, such as quaint shops and eateries that reflect the region's charm.Chittenden's locations offer a unique blend of relaxation and adventure, making it an ideal base for your holiday in Vermont.
Where are the best Chittenden ski resort rentals?
For renting ski accommodations near Chittenden, Vermont, the nearby Killington area is the most popular choice for winter sports enthusiasts. This region offers a range of rental options, from cosy chalets to spacious condos, all within easy reach of the slopes at Killington Resort, which is just a short drive away. Many properties in this area come equipped with modern amenities such as full kitchens, hot tubs, and fireplaces, providing a comfortable retreat after a day on the mountain.In Chittenden itself, travellers can find rustic cabins and lodges that allow for a more secluded experience. These often feature charming wooden interiors, ample living space, and outdoor decks, superb for enjoying the stunning winter scenery. Some cabins may also offer amenities like game rooms or proximity to snowshoeing and cross-country skiing trails for those looking to explore beyond downhill skiing.Additionally, the surrounding Green Mountain National Forest offers countless opportunities for outdoor adventure, with trails for hiking and snowmobiling that can be accessed from many rental properties.
What is the most popular type of holiday rental accomodation in Chittenden?
In Chittenden, holiday houses are the most popular type of holiday rental, with around 30 available in the area. These properties typically offer spacious living areas, fully equipped kitchens, and often feature outdoor spaces like decks or yards for enjoying the scenic surroundings. Many of these rentals are situated near the Green Mountain National Forest, making them ideal for outdoor enthusiasts looking to explore the natural beauty of Vermont.Additionally, there are several apartments and cottages available, providing more intimate options for couples or small families. These accommodations generally include essential amenities, allowing guests to enjoy a comfortable and convenient stay.
Are there any family house rentals in Chittenden?
In Chittenden, Vermont, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. The area boasts beautiful natural surroundings, with the Green Mountain National Forest nearby, providing ample opportunities for outdoor adventures. Many of these homes offer spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces for children to play and explore.Visitors can enjoy amenities such as Wi-Fi, laundry facilities, and sometimes even game rooms, ensuring a comfortable stay for all ages. Additionally, the proximity to local attractions like the Killington Resort and the charming villages of Rutland and Mendon adds to the appeal.
Are there pet-friendly house rentals in Chittenden?
In Chittenden, Vermont, there are several pet-friendly house rentals available, making it a great destination for travellers who wish to bring their furry companions along. The area offers a range of holiday homes that typically feature amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces like decks or gardens where pets can enjoy the fresh air. Many of these rentals are conveniently located near the picturesque Green Mountain National Forest, providing ample opportunities for outdoor activities such as hiking and exploring nature trails with pets.
Are there any remote work holiday rentals in Chittenden?
In Chittenden, Vermont, there are numerous remote work-friendly holiday rentals available, with around 33 options for travellers to choose from. Many of these properties are well-equipped to accommodate those needing to work while enjoying a getaway. Expect to find amenities such as free Wi-Fi, dedicated desks, and comfortable desk chairs, making it easy to stay productive.The charming surroundings of Chittenden offer a picturesque backdrop, with opportunities for outdoor activities like hiking and biking, superb for unwinding after a day of work. The area is also known for its proximity to the stunning Green Mountain National Forest, providing ample chances for exploration and relaxation. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Chittenden?
In Chittenden, popular rental amenities include fully equipped kitchens, which allow guests to prepare their own meals during their stay. Many properties also feature inviting fireplaces, great for warming up after a day of exploring the outdoors. Decks or patios are common as well, providing outdoor spaces for relaxation and enjoying the surrounding natural beauty. Onsite parking is typically available, making it convenient for those travelling by car. Additionally, some rentals come with porches or lanais, ideal for soaking in the tranquil atmosphere of this picturesque Vermont community.
When is the best time to visit Chittenden for a holiday rental?
The best time to visit Chittenden for a holiday rental is during the peak season from July to September. This vibrant period attracts travellers eager to immerse themselves in the stunning natural beauty and outdoor activities that Vermont has to offer. With summer in full swing, visitors can enjoy hiking, cycling, and exploring the picturesque landscapes, all while basking in warm temperatures averaging between 15 to 25 degrees Celsius.July stands out as the most popular month, bringing with it a lively option filled with travellers. The lush greenery and vibrant wildflowers create a superb backdrop for outdoor pursuits, making it an ideal time for those looking to engage in activities like kayaking on the beautiful nearby lakes or taking scenic drives through the charming countryside.For those who prefer a more tranquil experience, consider planning your visit in December. This month, while part of the low season, offers a unique charm with the onset of winter. The crisp air and snow-covered landscapes create a picturesque setting, superb for cosy getaways and enjoying winter sports.
What are the top attractions in Chittenden?
In Chittenden, Vermont, visitors can enjoy several picturesque attractions that showcase the beauty of the Green Mountains. The nearby Little Rock Pond offers a serene setting for hiking and fishing, making it a great spot for nature lovers seeking outdoor activities. The area is also close to the stunning Killington Resort, which is renowned for its skiing in winter and mountain biking in summer, offering a variety of recreational opportunities year-round.Chittenden is home to the beautiful Chittenden Reservoir, where guests can enjoy kayaking, paddleboarding, and picnicking while enjoying the scenic views. For those interested in local history, the nearby Norman Rockwell Museum provides insights into the life and works of the famous illustrator.
Are all fees included in the Chittenden holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Chittenden holiday homes with parking?
Stayz offers a wide selection of holiday homes in Chittenden with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Chittenden holiday homes?
You can find great discounts on holiday homes in Chittenden on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Chittenden holiday home booking on Stayz?
To find Chittenden holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Chittenden?
A long-stay holiday home in Chittenden is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Chittenden holiday home?
Book your Chittenden holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Chittenden?
Prices for holiday homes in Chittenden vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Chittenden to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

More holiday ideas